So being as I'l be carrying two mortgages come October 1st, I want to get a tenant in the house ASAP.Looking for a GREAT property management company in Chesapeake, Virginia Beach, Norfolk or Suffolk that is reasonable with their fees and will streamline the process on my end.  

For you the cash flow may not be as important, so you could shift towards investments that are more passive day-to-day.

I am thinking my biggest challenge in getting started is that my wife and I need to get on the same page as far as how to get started and the fact that I work an afternoon shift so its hard for me to go to local meet ups.

This could shift my focus to flipping but I really wanted to start building income for retirement.

Tenants have shifted their views, and feel much safer with their personal information stored secure online, than on a hand-written document in the hands of potential landlord that can be lost of stolen.Digital applications, leases, etc. are much easier to store securely and have on hand for whenever you need them! 

He thought he could come to my property after his 3pm shift and work for 2-3 hours and bang out the project in two weeks.

Outside of that, just plan on economies of scale (processes and streamlining) as much as possible and you will grow exponentially without missing a beat!!!

Perspectives and risk tolerance change dramatically as the Advil Age ensues :)By active to passive I mean a very natural and deliberate shift from owning properties and running a real estate investing business model that is very hands on and active in management and activity. 

Strategy shifts can take some time to think though and to execute.  

As of now my employment is keeping me VERY busy but will be shifting in the next month.